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“Does This Make Me Look Functional?” An At-Home Lipstick Challenge

At-Home Lipstick Challenge

Once upon a time, three million years ago (actually six), I tried to wear a different lipstick every weekday for a month. While working from home, popular wisdom tells us it can be helpful to maintain our normal routines, including grooming and getting dressed each day. And so, while I may have given up on real pants, I haven’t given up on lipstick…

Time spent at home is a good excuse to experiment with different looks, whether it’s trying a bold lipstick, finally learning how to apply eyeliner, or taking the time to master how to style your hair. I’ve even been considering a bold, impermanent hair color. Because why not?

To that end, here are five lipsticks I’ve worn while trying to be a person and failing working from home this past week. (Please forgive the at-home photography. I did my best!)

Lipstick Challenge

Day One: Sephora Cream Lip Stain in Always Red
My first choice is this vibrant, classic red, which looks like it belongs on the mouth of a person who means business. (I don’t particularly mean business today, but I still have to do business, and I’m hoping it will help me get the job done.) “Wow! Why do you look so great?” asks someone on a video call, before adding, “I haven’t changed out of these sweats in, like, a week.” I laugh and admit that if it’s any consolation, I am definitely wearing yoga pants outside the frame.

Lipstick Challenge

Day Two: Kosås Weightless Lip Color in Rosewater
After yesterday’s statement-making color, I reach for something softer. The name, rosewater, sounds like everything I want right now — cleansing, soothing, refreshing. That may be a tall order from a lipstick, but if any would be up to the task, it would be this blush pink nude. The color is very much your-lips-but-better. I keep it on all day and into the night, through many rounds of Nerts and multiple episodes of Succession.

Lipstick Challenge

Day Three: Charlotte Tilbury Matte Revolution Lipstick in Bond Girl
At this point, I am basically a gremlin that shuffles back and forth between the kitchen and the table, typing sentences and eating snacks. Thus, I choose Bond Girl, which stands hilariously at odds with how I feel. Worn full force, this color is a deep and dramatic berry. But I prefer it blotted on with my finger, where it takes on a pinkish-tawny hue that’s somewhere between a faun and a flower (sounds weird, but trust me on this).

Lipstick Challenge

Day Four: ILIA Color Block Lipstick in Tango
Today, I reach for the deep red Tango, hoping it may inspire a living room dance party. I don’t know if it’s the lipstick or listening to Brené Brown’s new podcast that does it, but I head out for a long, end-of-day walk, where I take in the shapes of the trees and the magnolias blooming on my block. For the first time in a very long time, I feel at peace.

An At-Home Lipstick Challenge

Day Five: MAC Matte Lipstick in All Fired Up
I choose this for two reasons: the color, which is a punchy, almost neon pink-red, and because “all fired up” is how I feel whenever I encounter the news. It does not make me more or less fired up, but it does make me feel strangely empowered on a terrifying conference call. (The other participants cannot see me, but it matters not.) As soon as the call is over, though, I wipe it off. This experiment has been fun, but as the night stretches ahead, I’m just as happy to lean in to being comfy for a while, in all my clean-faced, sweatpants-wearing glory.

At-Home Lipstick Challenge

Toni Morrison once wrote, “A dream is just a nightmare with lipstick.” Following this logic, if you add lipstick to a nightmare, does it become a dream? The answer is no. No, it does not. But it does make for a relatively light-hearted post, that I hope may entertain you during this bizarre time.

Have you found any beauty pick-me-ups lately? Or experimented with your look while at home? Please share!

P.S. The queen of lipsticks and another product that’s been a lifesaver lately.

Note: If you buy something through our links, we may earn an affiliate commission, at no cost to you. We recommend only products we genuinely like. Thank you so much.

  1. Elissa says...

    So excited to read that I am not the only one who does this! I have over 100 tubes of lipstick and needed to challenge myself and wear a different one each weekday too. You inspired me to do this even working from home. Cheers to lipstick! ??

  2. HH says...

    Caroline! You have inspired my dear friend (and also co-worker) and I to take this “challenge” and wear lipstick every day in April that we have video calls! If we aren’t going to be wearing our lipstick out to bars and restaurants, they might as well still get some play time! And it’s making us feel like real humans. Thanks for this fun idea :)

  3. A.J says...

    Growing from teens to twenties, my make up ‘regime’ consisted of lip balm and cheek blush. I discovered red lipstick at 30 and have not looked back since. Thanks Caroline for this post. I love all the shades of red you shared. :)

  4. Megan says...

    Wait is no one going to mention that your boyfriend is in the last photo?! Did I miss something or isn’t this the first time we’ve seen him?! So cute! Glad you’re happy, looking fab and have someone to hang with.

  5. Jill D says...

    The lipsticks are great and all, but I have to comment on Nerts! You are the first person I have ever heard of playing this game, and it is a huge part of our family holidays. I have several siblings and us, our spouses and older kids all get together (just like our parents, aunts and uncles did when I was a child) and team up and still have 7-9 decks of cards going. Sometimes the games last 20 seconds. It is so fun and am missing more than the three decks my husband son and I can do now.

  6. CARMEN GARCIA-GOMEZ says...

    During the Sarajevo’s siege, ( Balkans war) , women used to avoid getting out of the house without wearing their lipstick. Among the war correspondents was very well known the fact that even under the threat of the snipers and shelling, Sarajevo women used to put a lot of attention to their aspect. As you can imagine, getting out was a serious risk for everybody, but they did not have any option if they wanted to find some food or check if their relatives were ok (No Face time in those years!) I always admired their way to keep dignity even in times of war.

  7. Caz says...

    My lipstick collection has also been getting a workout recently! Most days working from home I’ve been makeup free and wearing leggings and a t-shirt. But to jazz things up, I’ve started doing Formal Fridays, where I put on a nice top (realistically still leggings on the bottom ;)) and do my hair and makeup. I find comfort in the ritual of putting on makeup, and the focus of carefully applying a bold lipstick or curling my hair is a nice moment of mindfulness.

  8. Stephanie says...

    Thanks for this post. It made me realize I should probably look more put together for my patient encounters via Telehealth and wear lipstick. It would probably be comforting for them to have their doctor look professional, competent, and badass during this scary time. They are struggling, so at least as their provider on the screen I should look like I can handle things on the exterior (even if I am scared and worried inside).

  9. All Fired Up is stunning on you, truly! Bold lipstick really does add a magical layer of fearlessness when working (especially in meetings). Thank you for a bit of beauty in the midst of chaos.

  10. Angela says...

    I am trying to reconnect with my naturally curly hair — I’ve been doing once-per-year session of Japanese straightening for at almost 20 years, though I never got around to doing it last year, so all but the last couple inches of my hair has grown out. Since I am working at home for the time being, I decided I didn’t need to bother with the weekly 45-minute hair drying/flat-ironing session. I am currently a messy, frizzy mess (in part because I didn’t have the right hair products), but am hoping to get a better result this weekend now that I have made a Target run that included hair products (and emergency chocolate). And if not … no one can see it but me!!!

    • Nancy says...

      Hi! I’ve been following curlysusie on YouTube for a few years. Her curly method is simple and beautiful! Cheers!

    • Jenna says...

      Ditto Curly Susie! So much great advice without overwhelm or huge investments.

    • Sarah Kyle says...

      The Curly Girl method is also really amazing and helped make my curls look (and feel) more healthy and beautiful. There are a lot of Instagram accounts out there for different wave/curl patterns and hair type, so you can have some guidance about what products and application methods might work best for your curls!

    • Kate says...

      Don’t brush it! I haven’t brushed my hair in 5 years since I went au naturale and it keeps the frizz away. Also highly recommend the Curly Girl Method ?

  11. Em Marie says...

    Love this bit of levity! If I may ask, where did you get the tee you’re wearing in the last photo? TIA :)

  12. rose says...

    LOL – I love these playful photo’s, thank you. They all look great on you of course. I love that rather subtly dramatic look of “modern geisha” where the lips are neutralized with a bit of foundation then color is finger blotted on with the deepest tone in the center and ombre’ing out to pale on the line. It’s so soft and fun for springtime. You can intensify it or naturalize it depending on mood.

    But what I’ve been obsessing over are video conference backdrops! I spent a hectic 20 mins creating a fricken amazing backdrop for an important meeting the other day – it’s radically improved my mood because that wall/worktop (behind my desk – but I sometimes also use the dining table) was a mess and now it looks like a magazine haha. I would have never done it if not for this new normal. Highly recommend a post on before and afters of easy video conference home backdrops!

  13. Rosie G. says...

    Charlotte Tilbury’s Bond Girl is my go to everyday lipstick. Hard color to describe; but, I love it. The only problem I have with Bond Girl is that it is very expensive. Last week I was able to get 25% off on this lipstick at a Nordstrom’s sale.

  14. J. says...

    I’m a person who draws immense comfort and peacefulness from routines, especially in the morning. My WFH situation (for which I am so immensely privileged) does involve being on video conference for at least 6-7 hours a day, so I use that as somewhat of an “excuse” (and the privilege/luxury of being only responsible for taking care of myself in this moment — I know this would be difficult to impossible with children!), but it has brought me tremendous comfort and joy to every single morning (going on day 16?) making my bed, showering, shaving my legs, putting on my full everyday makeup, jewelry, perfume, doing my hair, and putting on a sundress. My teammates comment laughingly (lovingly!), but I kept thinking back to this quote I read on a Cup of Jo beauty uniform years ago from a woman who had suffered something far more horrible than anything close to what I am facing — in describing her grief after she lost her husband, she said “put on mascara and lipstick every single day. That way, I could look in the mirror and see, ‘Oh, okay. There she is.’ If I could recognize myself, then my life felt recognizable.” This comfort of catching a glimpse of myself in the mirror (or upper corner of video conferences– I admittedly will check what I look like before a meeting begins!) and feeling “oh, okay– there I am” has brought comfort and a simple sameness/safety to my days when everything else about them has changed.

    And Caroline, you look beautiful in all of these! That first red looks like it was made for you — it would put such a smile on my face to see you on a walk or video conference with that flash of brightness!

  15. Elizabeth says...

    Good advice! I’ve been at home with my three children for what feels like years, and I pretty much wear my pajamas all day. No makeup. Hair stays more or less clean, but that’s it. It’s starting to feel like I‘m ill or something. When you don’t “fix up” (as we say in the south), it’s way too easy to climb back into bed. I didn’t realize how much I dress for other people until now!

  16. Alice says...

    This is so brilliant! I’ve been making a real effort to put on proper clothes- I’ve been wearing jeans and pretty tops, or dresses- always wearing a bra, though always wearing slippers too. Today I was SO tempted to put some pyjama bottoms on instead of jeans, but then remembered I had a video call with my boss-to-be (I start a new job in a month! Eeek!), so instead I put on my jeans AND eyeliner and mascara! Sure, I didn’t wash my hair this morning, but I still feel so functional as a result. It’s amazing what clothes and make up can do!

  17. Jill says...

    This post, while surreal, made me smile. Thanks for keeping up the light hearted content and razor sharp writing in such a strange time!

  18. Makeup has always been a great pick me upper.

  19. Lizzy says...

    How is the lipstick challenge six years ago?! I am shocked! I remember this vividly as if it were last year!

  20. Tarika says...

    That Bond Girl hippie looks so good on you! I’ve been on the fence about it, but now I’m convinced! I’ve been wearing tinted lip balms and Nudestix Nudies ‘in the nude’ on cheeks to perk me up. And Kajal! Never without kajal – it makes a huge difference!

    • SG says...

      I love love love my Bond Girl lipstick for the shade but fair warning, I find the formula a *bit* drying. You may not find that it is for your lips but that’s my one compliant about it. xxo

  21. Becs says...

    You look AMAZING in all of them!! Inspired me to try. ?

  22. sally says...

    I’m supposed to get married in June…overseas. Not sure what will happen, and I mostly feel frozen in terms of prep work at this point, but I have been wearing a different lipstick every day this week at home to figure out what color I might want to wear. I only wear non toxic products (like Kosas) and my coloring is the same as Caroline’s — any suggestions for a springy, rosey pink? I tend to like buildable, semi translucent options. Amongst current choices – Glossier Crush and Kosas Rosewater. I want to try Stardust too. Maybe Ilia Arabian Knights? HELP?

    • Elisabeth says...

      Kosas stardust is my go-to pretty peachy-nude pink.

    • Elisabeth says...

      I also recently tried a few Lily Lolo lipsticks. Their vegan lipsticks are almost as moisturizing as Kosas, “clean,” and come in a beautiful range. On my skin, Undressed is a lovely nude-pink that you might like, but there are a few “springier” pinks as well. The price can’t be beat!

    • sally says...

      Thank you so much, Elisabeth! Will have fun looking at those this weekend. I very much appreciate it.

  23. CS says...

    Well, even that little peek makes it clear that you two make a fine couple!!

  24. Sarah says...

    Earrings have been my version of this. Makes me feel like I got dressed and am ready for the day. Even if I’m still wearing leggings and a sports bra.

    • Ari says...

      SAME!

  25. Hali says...

    I put on makeup today for the first time in quarantine!! It’s been weeks now… I think? Damn my face was BARE. My eyelashes were so clean they almost disappeared. I am not the type of person to swipe mascara on before leaving the house anyways, I usually do not care for makeup or hair maintenance unless I’m intentionally about to go see someone I know. If I happen run into friends at the grocery store, they get Grocery Store Hali. IDK I just don’t care? So quarantine has been all about super clean skin and hair that is clean but reallll messy.

    WOAH! A little brow love, some shimmer on my cheeks and a dose of mascara… my face came ALIVE! I’m sitting a little taller in my desk, I’m more alert, I feel better over all. I’m shocked by the effects of this practice.

    I must note that my husband has so far made no notice of the makeup. He did not blink at all, zero reaction. I genuinely think he can’t see a different.

    I can’t tell if this bothers me or delights me.

    • Claire says...

      I love this comment! I was getting really good at liquid eyeliner about two weeks ago (if I tight line top/bottom lashes, they look natural but super awake) and now I couldn’t be bothered. Yesterday, with literally fifteen seconds to spare before getting on a call with my boss, I realized I wasn’t wearing a bra under the pajama shirt I was still wearing. At 12pm. This is getting bad. Tomorrow I will shower and wear clothes by 9am, I swear.

    • Natalie says...

      this last bit made me chuckle. i wore a dress yesterday instead of the ever present sweats and assumed my boyfriend would notice. nope.

    • Alex says...

      Ha!

    • hali says...

      Claire! I wrote off liquid liner years ago because as I mentioned, usually I’d never be bothered to put it on except right before walking out the door, which we all know is the worst time to put on liquid eyeliner.

      If there was ever a time to perfect twin winged eyes… it would be every single night before dinner for the next month. I just need to find whatever liquid eyeliner I still have that’s been neglected for months.

      Thanks for the idea! Also, It’s 2pm and i’m not wearing a bra still.

  26. Laura M. says...

    Real life me is kind of low maintenance and has been known to go out in public looking like a gremlin. But social distancing me, well she puts on lipstick and fully gets ready every day. I’m even wearing jeans as I type this. I’ve challenged myself to wear all my lipsticks and to try different outfits for as long as this lasts. This is my way to take care of myself, express some creativity, and hopefully build some cute habits that will come in handy when we’re allowed to socialize again.

    • Jenny says...

      This sounds like such a nice strategy! ❤️❤️

  27. Ceridwen says...

    Love this! My sister in law and I have been talking about the power of lipstick at home. She put on a Stilla bold red like out muse Alison Roman, and after a very hard day, felt like a warrior princess ready if for anything!

  28. Julka says...

    Oh, I love this idea! I always wanted to try to feel comfortable wearing lipstic (especially some bright, daring color and feel like a movie star!) but never found courage. I adore women who do that, so quarantine feels somehow like a perfect time to start! I will wear some red lips at home first, and then hopefully outside too!

  29. Bekky H says...

    This post made me smile. Thanks!

    • Jenny says...

      Thank you for this beautiful post. The kind of post I needed today. More of these! And love your work and attitude Caroline ❤️❤️

  30. Madeleine says...

    Lovely post- and it’s as if you read my mind. Was just thinking this evening that tomorrow I will crack out some lipstick for exactly this reason. Thank you, Caroline. X

  31. Lara says...

    Oooh they’re all so pretty! Rosewater is my personal favourite in the photos here – it really suits your skin tone – but they’re all gorgeous on you.

    And yes to not giving up. I’ve been working from home for almost a year now and my daily routine, which takes about 30 minutes, includes: showering, shaving lower legs and underarms, and putting on jeans (stretchy, of course!) and a smart but comfortable long-sleeved tee, then a light touch of makeup including lip stain, tinted lip balm, BB creme, a bit of Touche Eclat, a swipe of blush and a little brow pencil. I also wear a piece of jewellery every day.

    For something that takes so little time and effort it makes me feel a million times better, even if I don’t leave the house.

  32. J says...

    Great post – exactly what I needed. I looove Bond Girl, the Kosas is lovely, and the Sephora red is WOW. I’ve been putting on make up most days too, it makes me feel more like the lady in charge of my domestic catastrophe :D

    I’ve been torn on ordering more WFH pants – a new pair of leggings and some jogger type pants. I don’t want to add to the burden our postal and delivery workers are suffering under right now. I love being able to order everything, but I hate the crappy ethics of Amazon and UPS and even USPS (they aren’t the good employer they used to be). Am I being too squeamish for my own good?

    • Amy says...

      I’m right there with you – I had decided to only order essentials and to lump purchases and avoid Amazon as much as possible. So far I’ve only ordered a refurbished Kobo (e-reader) for my bookworm daughter that’s compatible with our library system, and one gift for my son’s birthday – but those don’t seem like essentials like food and toothpaste. Where does one draw the line?

      It puts people at increased risk and as an employee of a local foods home delivery service, I know how nutty and risky it is out there right now (and on the flip side, I’m the one adding more cookies and fun things to the site because I know it might brighten a day and I’d rather people stay home than go out for fun!)

  33. Chandra says...

    You look beautiful and love seeing your boo!

  34. Sarah says...

    I’m trying to get dressed every day. I’m definitely keeping the place clean and cooking and baking. It’s not getting me down yet, but I kind of feel like the quarantine has chipped a little off my humanity. I’m fighting back by keeping my space as pleasant as I can muster!

  35. Hannah says...

    I will never wear another lipstick that isn’t Kosas. I’ve always wanted to be a lipstick girl, and their formulas are so amazing and not-drying! Stardust is my jam.
    And as far as what I’ve been experimenting with, I’ve used face oils for awhile, but just got Everday Oil to see if a more heavy-duty formula will help with my extremely dry pregnancy face. It smells so good! You can use it as a face wash/moisturizer and that’s all I’m doing to my face right now. I also ordered cute slippers for schlepping around the house in.

  36. Alexis says...

    I’m fortunate enough to be able to work from home.
    I have not tried anything new, but I do still shower each morning and get dressed. I worked at a creative/startup prior, and am now in philanthropy where it’s business casual (no sneakers, AHHHH)!
    I bought a bunch of new shoes so I am using this opportunity to break them in by wearing them around the house (don’t worry, the are NEW i.e. never touched the pavement).
    We’re also trying to figure out our hair as a family. I have to cut my partner’s hair and he will try to cut our son’s hair. Any tips would be much appreciated. On the bright side tho, no one’s gonna see our hack jobs for a while!

    • Hannah says...

      I’m following this for tips! I tried to cut my husbands hair a couple years back bc my best friend swears by it. We decided to shell out the extra cash and preserve our relationship after 2 attempts :)

    • E says...

      I cut my own hair and my boyfriend’s hair. I give myself an undercut and then try to layer the rest of my hair. My hair naturally looks like Cousin It, but I mostly wear it in a bun.

      Cutting your own hair is hard! My best tip is just to really get your mirrors going–I’m lucky to have a medicine cabinet with mirrors on the inside of two doors. But you have someone else at home so maybe they can hold up mirrors for you :).

      Also, be gradual and try to go back and forth between sides so you don’t end up really lopsided.

      When you’re cutting someone else’s hair, using a guard on an electric razor is the best way to get an even cut (I think). Much harder with scissors. We use my boyfriend’s beard trimmer for his haircut and my undercut.

      Also when cutting someone else’s hair, try to figure out the “corners” of their skull before cutting. Typically you want the overall shape of the haircut to follow the skull somehow…. with men, that’s usually shorter on the sides with a bit longer (or a lot longer, as is kind of fashionable now) on top. And you want to fade the “corners” (where the vertical and horizontal meet).

      If you are using any electric shaver, remember that cutting against the direction the hair’s growing does a MUCH shorter cut than going WITH the hair.

      Hopefully this will help — from one amateur to another :)

  37. tina crisas says...

    You look just beautiful in all of them, and those eyelashes, wowza! Also, a photo of the two of you!! What a gorgeous couple you guys are!!! Like, seriously!

  38. Kate says...

    100% the kind of post I needed to see today — thanks for brining some fun to this weird lock-in experience!

  39. ks says...

    this post had me cheekily googling how old caroline is – I’m having skin envy. here’s to wishing that she’s a child prodigy = ;) (according to when she graduated college she is 3 years older than me). caroline – i’m emoji clapping to whatever routine you’ve got going on. left this article with a much needed laugh and pick-me-up and a deep google into masks & skincare! haha! xx

  40. Carrie says...

    Ugh, we get it…you are gorgeous :p And Bond Girl if my fav although they all look beautiful on you!

  41. Jessica says...

    All my life I have never ever put in the effort to style my hair beyond blowing it dry and a little product for volume. I literally just now bought a Revlon rounded blow brush (I think that’s what it’s called?) and I’m going to figure it out!

  42. Sonja says...

    You are a lovely writer and this post hit just the right tone – thank you for making me feel good in the middle of everything! You rock! :)

  43. Mimi says...

    I keep trying bold lip colors but they always look so shocking. Since I’m getting older I’ve noticed my brows are getting sparse beyond my arch. Makeup has never been my forté but I feel like something needs to be done. Now that I’m not going out of the house I figure it’s a perfect time to experiment. I did my makeup, because that always makes me feel better when I’m sad/depressed/feeling especially insecure, and I finally found my answer to brow makeup – brow powder! I don’t really like wearing makeup, but I might just start wearing makeup everyday! My husband even gave me a compliment. :)

  44. Katie says...

    I’m doing more masks than usual! Some things I had around (tara Harper resurfacing is my favorite!) but I’m looking to expand my horizons. Any recs? Particularly looking for anything that feels really good, as a ritual. Something nourishing. Also anything that can make my pores smaller/help with texture. Doesn’t have to be the same mask!

  45. Julie says...

    Love number 4!

  46. Sarah says...

    Could you please do a post on how to look alive/professional/not dead/less wrinkly on Zoom/other virtual meeting platforms?? I feel like the person I’m seeing in my screen doesn’t look like the person I see in the mirror. HELP!!

    • Katie Woodward says...

      It’s not you! Try to get the camera to eye level (maybe a stable couple of stacks of books to prop up a laptop) and work on the lighting. If its during the day, facing a window is great! If not put a lamp on either side of the computer. Translucent shades rather than opaque are best! Get rid of the overhead lighting. Hope this helps!

    • Alexandra says...

      Great tips Katie! Thank you :)

    • p. says...

      also in zoom under video settings, there’s an option to touch up your appearance. (I learned about this from the Q&A in the Sunday NYT business section.)

    • Audrey says...

      Love your tips, Katie! And totally agree with them all. I’ve been doing Zoom meetings for years and it’s amazing what facing natural light will do. That and a little lip gloss ;)

    • Wyn says...

      “Touch up my appearance” option – whoa. Thanks for the tip, P!

    • Katie says...

      Weird things I didn’t realize my theatre degree prepared me for ?

  47. Amanda says...

    Has anyone else been obsessed with their skin since starting isolation? Yesterday I noticed a clogged pore and proceeded to poke and prod it until it became a dime-sized bruise in the middle of my forehead that I swear must have been noticeable even when the Zoom camera was off… just me?

  48. MK says...

    I have never been a lipstick person- then I discovered Glossier Generation G in cake and I’m hooked. It goes on incredibly easily and stays put without feeling like it’s shellacked on. The color is perfect for every day, and it’s buildable, which I really love.
    Makeup has definitely helped these days- most quarantine days I have gone without, but today I put some on and it felt great. I will probably continue to do whatever feels good to me, whether that’s makeup or no!

  49. Alexandra says...

    Caroline, thank you thank you for this light-hearted post during this bizarre time! You are a beautiful writer and it’s so comforting to read about something fun like lipstick amidst all the scary news out there.

  50. Carolyn says...

    “At this point, I am basically a gremlin that shuffles back and forth between the kitchen and the table, typing sentences and eating snacks.” Lol lol lol, thank you for the laughs this morning Caroline, much needed. And you can definitely rock a bright red bold lip!

    • Don says...

      This speaks to me deeply rn.

  51. Francine Schlesinger says...

    Can you tell me what breed your little poochie is? So cute!

    • Caroline Donofrio says...

      Thank you! She’s a Yorkie/Maltese mix. :)

  52. Boerumama says...

    I have a bored teenager with dark brown hair who wants to experiment w/ a semi-permanent hair dye. Since you mention dying–any recs for brands etc? She wants to go auburn. Thanks!

    • Mimi says...

      Very fun! From personal experience, semi-permanent color does NOT just was out. It fades, but there will always be color left – is your daughter is ok with this?
      Clairol’s Natural Instincts Demi-permanent doesn’t have the harsh chemicals that permanent dyes do and it fades/blends nicely. Any out of the box color is going to cause some element of damage, but Natural Instincts is pretty gentle and super easy – just be sure to do a patch test to rule out allergic reactions.

    • Emma says...

      If she wants to go auburn, I’d highly highly highly recommend trying Lush’s Caca Rouge Henna dye. It’s natural and gentle on hair, leaving it soft and healthy and conditioned rather than fried. The color color stains the hair rather than totally transforming it, and will slowly fade over time. I dyed my hair red for years and switching to henna totally saved my hair.

    • Cynthia says...

      I used to use Clairol Natural Instincts until I decided to embrace my gray. I found it was best to buy one shade lighter than what I wanted for the final result. It gradually fades over time.

    • Boerumama says...

      thanks for your suggestions about this, everyone! this’ll occupy us for at least a couple of hours.

  53. Sophie says...

    The Sephora Lip Stain looks amazing! Did it wear well throughout the day? I find that some stains dry out my lips or end up looking rough in a few hours. I would love to know your thoughts on this one!

    • Caroline Donofrio says...

      Yes, this one wears well and has absurd staying power. As long as your lips are pretty smooth when you put it on (I’ll sometimes buff mine with a washcloth first to remove any rough patches), it wears pretty solidly through eating, drinking, talking, etc. and comes off easily with a little makeup remover (or just plain coconut oil). It can be a little drying, but I find it’s nothing that sleeping with a good lip balm won’t fix!

  54. Anne-Marie says...

    The Bond Girl looks really fabulous on you! Thanks for a fun post.

  55. Michaela says...

    You are so pretty and that couple pic is adorable. I think it’s the first glimpse we’ve seen of the two of you on here and it gave me such a burst of joy for you to see it (and I mean that in a CoJ fan club from across the interwebs way). I hope you two are happy (or as happy as one can be) social distancing together!

  56. Robin says...

    I love the Kosas one, but Caroline, lipstick looks great on you- just in general. Also: Yes to the Brené Brown podcast. And I am also finding great comfort in Sunstorm.

  57. Rosewater and Bond Girl are gorgeous on you! Right now I’m skipping foundation and blusher and just going with simple eyes and lipstick. I’m using lots of moisturizer and eye cream. Loving Cerave Daily Moisturizer and L’Oreal Age Perfect Rosy Tone Anti-aging Eye Cream. Keeping it simple.
    I feel so much better to put on make-up and look presentable, even if it is only to wave to the delivery people and FaceTime with my kids.

  58. Chrissy says...

    You look gorgeous in all of them!

    How do you know if a shade will look good on you since you can never know how it’ll look until it’s on your lips? For me, trying on lipsticks at a retail store doesn’t work because of germs. And meanwhile shopping for lipstick online is a gamble because the shade will appear differently on the screen.

    • Caroline Donofrio says...

      Thank you! My trick is to pay attention to the undertones, vs. the actual shade. For example, I know that most reds work on me, but that some cool tones or colors with brown undertones do not, so I keep that in mind when browsing. Also, if a color isn’t what I hoped it would be, I’ll mix it with another shade until it skews in a direction that works for me. Last but not least, some retailers (like Sephora) let you return cosmetics (even if they’re gently used!) for a full refund.

  59. Amanda says...

    I love this! I’ve found that my self care routine has actually improved since working from home because when I cut out my 3-4 hours a day of commuting, I can sleep in a little and fit in regular (online) workouts. I’ve been waking up, washing my face, exercising, washing up, getting dressed and putting on lipstick. Lipstick is the only makeup I ever wear (unless I’m being super fancy) but I wear it every single day. I’ve definitely gotten the same types of comments about it in video meetings.

  60. Meg says...

    In my experience lipstick (like fragrance) is super individual. What appears natural on one person, may appear orangish on another.

  61. Mindy says...

    What mascara are you wearing? Especially in your last pic! TIA!

    • Caroline Donofrio says...

      I’m wearing W3LL PEOPLE Expressionist volumizing mascara, in all photos.

  62. Jean says...

    Your brows! Your lashes! Any tips or insights you can share with us? This was a fun read, thank you.

  63. Anouschka Defraeye says...

    I have dozens of colours of eye shadow. Some of them I’ve never used. So to cheer me up each morning, I pick a different colour every day :). To day it is purple, yesterday it was grey + fuchsia …

  64. Christina says...

    YOU ARE SO PRETTY! Thanks for a wonderful post.

  65. Amy says...

    You’re so pretty!

  66. SlyBK says...

    your “crappy at home photography” equals my “paying someone to take headshots and photoshop the hell out of my face” … or more simply put: you look gorgeous!

  67. Chelsea says...

    I love this idea! I’m definitely going to do this for the rest of my WFH time.

  68. Laura says...

    Love this – but what is the lipstick in the last pic (the couple shot)?

    • Caroline Donofrio says...

      Thank you! That’s Bond Girl!

  69. Frankie Rose says...

    Sorry for the double comment but it might be helpful to hear from a “brow expert” on how to groom your brows at home. Mine need some help and there’s not an end in sight yet. Just thought about that while looking at Caroline’s perfectly groomed brows!

    • Christina says...

      Frankie Rose, I am using this as an opportunity to let my brows grow in fuller! I look a little like Oscar the Grouch, but I have confirmed you can’t really see it on FaceTime. I was inspired by this post by Stella, when she let her brows go for a year (!) and changed their entire appearance.
      https://cupofjo.com/2016/09/eyebrow-before-and-after/
      For now, I’m letting things go on their own, and maybe in another month I’ll do some light tweezing. :)

    • Rae says...

      Adding to Christina’s comment—I’m four months into growing my brows back. Below is a very helpful and detailed article from brow expert Kristie Streicher, if anyone would like to read. Don’t give up and you’ll see results. The four month time is when you really see them starting to grow back to their pre-90s glory.

      https://www.violetgrey.com/violet-files/beauty-lessons/how-to-get-your-brows-back

    • Frankie rose says...

      Thanks for the recs! However, I already have full eye brows that needs to be shaped (actually similar in size and shape when groomed) to Caroline’s otherwise they take over my face!

    • Amy says...

      After reading Stella’s post, I let my eyebrows grow out for a full year. Seriously.

      I accrued about 7 stray hairs that weren’t connected to my actual eyebrows. Finally I accepted that no more were coming in to fill the gaps, and plucked the loners.

      I plucked my eyebrows religiously in high school (2001-2005), although thankfully I recognized that they don’t usually grow back and I didn’t go to the extremes we were seeing back then.

  70. Claire says...

    I just put on a pretty pink shade for a zoom meeting!!! LOL, lipstick for the win!

  71. Frankie Rose says...

    This is content I need right now! A fun distraction. It’s funny- I’m working from home and have a 22 month old and live in a super small space where it still feels like winter (bleak, grey) but getting up, showering, putting on some easy makeup is really helping me. I’m actually doing more than I do when I’m out in the world and this experience is helping me realize the power of how good it feels to feel put together. I’ll definitely take this with me after this is over and spend some more time and care on myself. Thank you for this! Loving the Kosas- I might purchase! Xoxo

  72. Annette says...

    Caroline – Which lipstick are you wearing in the last picture (the cute couple pucker picture)?

    • Caroline Donofrio says...

      That’s Bond Girl!

  73. I’m making sure to put on mascara. It’s easy to slide into sloth right now and at least this will make me wash my face before going to bed. And, well, I do look better with mascara even if I’m the only one seeing me.

  74. Hannah says...

    You look beautiful! Lipstick makes everything better.

    • Judy says...

      This post really lifted my spirits down here in Sydney, Australia where we’re seeing exponential rises in case numbers and things just seem so…much. Thanks Caroline xo

  75. G says...

    This is too funny because just the other day I thought to myself “maybe I should wear lipstick while working, just to make myself feel a bit more primp&proper in my pjs.” But then, when I woke up the next morning I was already so overwhelmed that I decided to skip it. I’m glad to see I was on the right path though, and might try wearing some one of these days.

  76. Liz says...

    One of the many things I love about CoJ is your ability to have fun, lighthearted posts amidst the craziness of life without it feeling like you’re ignoring what’s happening in the world. Thank you for addressing the challenges many of us are facing and still giving us a space to talk about makeup and hair styling :)

    • Megan says...

      This, exactly! It acknowledges the terrifying surreality of the current situation while still giving me some laughs (and good content re: lipstick. and a cute couple photo!). Thanks Caroline!

  77. AB says...

    Caroline, you wear these so well. Thanks for the pick-me-up. Can I ask where you necklaces are from? They’re gorgeous!

    • Caroline Donofrio says...

      Thank you! The beaded ones are tiny opal beads I found on Etsy, and the rose quartz triangle is from Satya, a few years back.

  78. Allie says...

    Any suggestions for avoiding feathering/bleeding with these fabulous colors? I use a liner and still feel like I look like a clown at the end of the day.

    Thank you for this lighthearted post!

    • Caroline Donofrio says...

      I find my lipstick wears better if I put on a very light coating with my finger or a brush first, then blot it, then follow it up with another light coat, and blot it again (vs. applying it straight from the bullet). You can do this as many times as you like until it reaches your desired shade. When I’m done, I’ll also blend it in near the edges, using my finger. The more it sinks in, the less it can bleed. Hope that helps!

    • Amanda says...

      The only makeup I wear is lipstick, but I wear it every day. As I’ve gotten older, feathering has definitely been more of an issue. Liner helps, and so does primer. I use an inexpensive drugstore primer from Nyx, which works well, and weirdly, kind of smells good. There are also fancier ones, like Mac prep and prime for lips. Like Caroline, I usually apply, blot, apply, blot again. And of course, some lipsticks are just worse about feathering than others. Unfortunately for my lips, the ones that stay on the best are usually the dry matte ones rather than rich/creamy/moisturizing. So at night I usually slather on something moisturizing before I go to sleep.